I haven't ridden in ohh at least thirty years
so Shank's pony it is.....and even though I walk about barefoot in my home and garden, even I wore shoes when I worked where Tengu is now.
Wet's the issue with shoes, which is why the courrans/sandals are sort of effective, but unless you use very fine, and thus not terribly strong, leather, then they really needs socks of some kind beneath them. Even Oetzi had shoes, though his were stuffed with soft grass.
Picked clean fleece is very good, it felts down beautifully, is warm and comfortable, and if you leave the lanolin in it doesn't stay as wet.....ends up stinking though, while the grass doesn't.